PMID- 926117
OWN - NLM
STAT- MEDLINE
DCOM- 19780127
LR  - 20191210
IS  - 0022-2623 (Print)
IS  - 0022-2623 (Linking)
VI  - 20
IP  - 9
DP  - 1977 Sep
TI  - [1-(L-2-hydroxy-3-mercaptopropanoic acid)] analogues of arginine-vasopressin, 
      [8-D-arginine]vasopressin, and [4-valine,8-D-arginine]vasopressin.
PG  - 1173-6
AB  - [1-(L-2-Hdroxy-3-mercaptopropanic acid)]arginine-vasopressin (hydroxy-AVP), 
      [1-(L-2-hydroxy-3-mercaptopropanoic acid),8-D-arginine]vasopressin 
      (hydroxy-DAVP), and [1-(L-2-hydroxy-3-mercaptopropanoic 
      acid),4-valine,8-D-arginine]vasopressin (hydroxy-VDAVP) were synthesized by a 
      combination of the solid-phase and solution methods of peptide synthesis. 
      Protected octapeptides synthesized by the solid-phase method were further 
      acylated by 1 + 8 couplings in solution to furnish the key intermediates. 
      Hydroxy-AVP has antidiuretic potency of 470 units/mg and activity in the rat 
      vasopressor assay of 550 units/mg, representing a small enhancement of activity 
      over that of arginine-vasopressin (AVP) in each case. Hydroxy-DAVP and 
      hydroxy-VDAVP have essentially the same high antidiuretic activity (900 units/mg) 
      and very low vasopressor potencies (0.9 and less than 0.02 units/mg, 
      respectively). Hydroxy-AVP, hydroxy-DAVP, and hydroxy-VDAVP thus have 
      antidiuretic-pressor selectivity (A/P) of 1, 1000, and greater than 45 000, 
      respectively. These data are compared with those of other vasopressin analogues. 
      Hydroxy-VDAVP is a highly specific antidiuretic peptids and may be useful in 
      pharmacological studies of antidiuresis.
FAU - Lowbridge, J
AU  - Lowbridge J
FAU - Manning, M
AU  - Manning M
FAU - Haldar, J
AU  - Haldar J
FAU - Sawyer, W
AU  - Sawyer W
LA  - eng
PT  - Comparative Study
PT  - Journal Article
PT  - Research Support, U.S. Gov't, P.H.S.
PL  - United States
TA  - J Med Chem
JT  - Journal of medicinal chemistry
JID - 9716531
RN  - 11000-17-2 (Vasopressins)
RN  - 113-79-1 (Arginine Vasopressin)
RN  - 52049-52-2 (argipressin, Val(4)-)
SB  - IM
MH  - Arginine Vasopressin/*analogs & derivatives/chemical synthesis/pharmacology
MH  - Diuresis/drug effects
MH  - Structure-Activity Relationship
MH  - Vasopressins/*analogs & derivatives
EDAT- 1977/09/01 00:00
MHDA- 1977/09/01 00:01
CRDT- 1977/09/01 00:00
PHST- 1977/09/01 00:00 [pubmed]
PHST- 1977/09/01 00:01 [medline]
PHST- 1977/09/01 00:00 [entrez]
AID - 10.1021/jm00219a012 [doi]
PST - ppublish
SO  - J Med Chem. 1977 Sep;20(9):1173-6. doi: 10.1021/jm00219a012.